Chris Rock has such a warm, magnetic presence that it's baffling that he has never seemed that comfortable as an actor. Cutting and ferocious as he may be onstage, onscreen he often comes across as timid, like he doesn't belong. (It's telling that when I think of his film career, the first thing that comes to mind is his work in the Madagascar films, which just requires his bug-eyed-crazy voice.) Rock showed such promise after stealing New Jack City almost 25 years ago, but since then, he's struggled to establish himself as a comedic or dramatic force at the movies.

That all changes with Top Five, where he serves as writer, director, and star. In interviews, Rock has said that he worked on the screenplay during his downtime while co-starring in Grown Ups 2; if that's the case, then we finally have a reason to be grateful for that atrocious Adam Sandler debacle, as it provided his buddy with a chance to focus on a comedy that has a little depth to it while still being wildly, rudely funny. Rock often talks about his love of Woody Allen movies, and through that prism, Top Five might be his Stardust Memories. But Woody never tackled celebrity with this kind of lightness, and he also never came up with an astounding/disgusting joke about cum-stained sheets.

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Rock plays Andre Allen, a successful stand-up and movie star whose film career is mostly built on a terrible franchise called Hammy the Bear. (Andre dresses up in a bear costume for the action-comedies, delivering the series' catch phrase, "It's Hammy time!" while firing AK-47s.) But now he wants to be taken seriously and has thus gotten involved in Uprize, an Oscar-bait drama about the Haitian Revolution; Andre hopes he can change his image, even if every interviewer and fan just wants to know when the next Hammy film will start shooting. (One of Top Five's best subtle touches is that, wherever Andre walks in New York, we can very faintly hear people in the distance saying variations on "Hey, Hammy!" It's a soundtrack of constant adoration, but also irritation, for the character.)

The movie's narrative engine comes courtesy of Chelsea Brown (Rosario Dawson), a New York Times interviewer who will be following Andre around for the day. Andre hates the Times because it has always eviscerated his films, but Chelsea insists that she doesn't share the critics' dim view of his work: She wants to give him a platform to explain himself and promises to be fair.

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It's a sign of Top Five's sophistication that while, in theory, it's a romantic comedy, I didn't spend a lot of time wondering if Andre and Chelsea were going to end up together. Rock's film—his third as a director, following 2003's Head of State and 2007's I Think I Love My Wife—wanders in a such a pleasantly loosey-goosey fashion that you think of the main characters as people with interesting lives and nuanced personalities, not as folks who are being shoehorned into a formulaic plot. Andre and Chelesa have very different lives—he's a celebrity about to marry a reality-TV star (Gabrielle Union), while she's a single mom trying to make a living as a writer—but they don't feel diametrically opposed in that sitcom-y, meet-cute kind of way. Their conversations are filled with ribbing and zingers, but it's also playful and grownup, like the way actual human beings speak.

I Think I Love My Wife was a remake of French filmmaker Éric Rohmer's Love in the Afternoon, and there is a slightly Rohmer-esque quality to Top Five's extended dialogue scenes. (That could also be the Woody Allen influence, too.) But Rock keeps his storytelling tight, using flashbacks to Andre's earlier career to show how he got to where (and who) he is now, a recovering alcoholic who wants to finally settle down, even if he's not entirely sure that his fame-obsessed fiancée is right for him. (In a movie that's fairly compassionate to its characters, Union is stuck playing a reality-star freak show, never able to embody more than a noxious cliché.) Andre may have overdone his bid for artistic legitimacy, but Rock doesn't: Top Five is articulate about the ways that people's choices trap them on certain life paths, but it's executed with such spirit that it never feels self-consciously "serious."

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Of course, it also helps that the movie is so damn funny. The attacks on the reality-TV world are pretty toothless, and for a guy who's been in the industry for a long time, Rock gets a lot of the small things wrong about Hollywood and entertainment journalism. But unlike a lot of studio comedies, where you know where you're going from the first second, Top Five gets stronger as it rolls along. In part, that's because it was made outside of the studios: Though backed by Oscar-winning super-producer Scott Rudin, Rock made the film independently, inspiring a big bidding war after its premiere at the Toronto Film Festival. Not surprisingly, this is the only studio-released movie of 2014 that talks this frankly about race, class, hip-hop, addiction, and the weird sexual hangups some people have. Plus, Rock doesn't just cast his famous buddies, but gives them something to do: Everyone from Adam Sandler to Tracy Morgan to Leslie Jones to Sherri Shepherd isn't just funny but really good, no matter how small the part.

To tell the truth, though, Rock still doesn't seem like a natural leading man: His jittery, solitary stand-up energy doesn't quite mesh with the ensemble work going on in here. But what matters is that he makes you laugh while also making you care about this guy. For sure, this is his most complete performance onscreen, sexy and subdued without trying to be "on" all the time. Nearing 50, Rock has made a movie that's aimed at adults while still being raunchy and unwieldy enough that it's not boring. And for a film whose unpredictable energy makes it hard to guess its next move, Top Five nails its ending—which, I only realized after the fact, was where we were headed the whole time.

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Grade: B+

Grierson & Leitch is a regular column about the movies. Follow us on Twitter, @griersonleitch.